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30636-90-9,MFCD12032048
Catalog No.:AA0030ND

30636-90-9 | Dammar-24-ene-3,12,20-triol, (3β,12β)-

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50mg
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100mg
analytical standard,≥98%
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0030ND
Chemical Name:
Dammar-24-ene-3,12,20-triol, (3β,12β)-
CAS Number:
30636-90-9
Molecular Formula:
C30H52O3
Molecular Weight:
460.7321
MDL Number:
MFCD12032048
SMILES:
CC(=CCC[C@@]([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)(O)C)C
Properties
Computed Properties
 
Complexity:
783  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
4  
XLogP3:
7.2  

Literature

Title: 20(S)-protopanaxadiol (PPD) alleviates scopolamine-induced memory impairment via regulation of cholinergic and antioxidant systems, and expression of Egr-1, c-Fos and c-Jun in mice.

Journal: Chemico-biological interactions 20180105

Title: Production of rare ginsenosides (compound Mc, compound Y and aglycon protopanaxadiol) by β-glucosidase from Dictyoglomus turgidum that hydrolyzes β-linked, but not α-linked, sugars in ginsenosides.

Journal: Biotechnology letters 20120901

Title: Cytochrome P450 CYP716A53v2 catalyzes the formation of protopanaxatriol from protopanaxadiol during ginsenoside biosynthesis in Panax ginseng.

Journal: Plant & cell physiology 20120901

Title: Conversion of protopanaxadiol type saponins to ginsenoside Rg3 by lemon.

Journal: Natural product communications 20120901

Title: Fungal sensitivity to and enzymatic deglycosylation of ginsenosides.

Journal: Phytochemistry 20120601

Title: A novel oral dosage formulation of the ginsenoside aglycone protopanaxadiol exhibits therapeutic activity against a hormone-insensitive model of prostate cancer.

Journal: Anti-cancer drugs 20120601

Title: Determination of 20(S)-protopanaxadiol ocotillol type epimers in rat plasma by liquid chromatography tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120301

Title: Kinetics of a cloned special ginsenosidase hydrolyzing 3-O-glucoside of multi-protopanaxadiol-type ginsenosides, named ginsenosidase type III.

Journal: Journal of microbiology and biotechnology 20120301

Title: Protective effect of ginseng sapogenins against 2,2'-azobis (1-aminopropane) dihydrochloride (AAPH)-induced LLC-PK₁ cell damage.

Journal: Bioorganic & medicinal chemistry letters 20120101

Title: The in vitro structure-related anti-cancer activity of ginsenosides and their derivatives.

Journal: Molecules (Basel, Switzerland) 20111219

Title: Snailase preparation of ginsenoside M1 from protopanaxadiol-type ginsenoside and their protective effects against CCl4-induced chronic hepatotoxicity in mice.

Journal: Molecules (Basel, Switzerland) 20111206

Title: The Cyt P450 enzyme CYP716A47 catalyzes the formation of protopanaxadiol from dammarenediol-II during ginsenoside biosynthesis in Panax ginseng.

Journal: Plant & cell physiology 20111201

Title: 20(S)-Protopanaxadiol, a metabolite of ginsenosides, induced cell apoptosis through endoplasmic reticulum stress in human hepatocarcinoma HepG2 cells.

Journal: European journal of pharmacology 20111001

Title: Acylated protopanaxadiol-type ginsenosides from the root of Panax ginseng.

Journal: Chemistry & biodiversity 20111001

Title: Anti-cancer effects of 20(S)-protopanoxadiol on human acute lymphoblastic leukemia cell lines Reh and RS4;11.

Journal: Medical oncology (Northwood, London, England) 20110901

Title: Cell-type-specific regulation of raft-associated Akt signaling.

Journal: Cell death & disease 20110401

Title: Identification of 20(S)-protopanaxadiol metabolites in human liver microsomes and human hepatocytes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110301

Title: Production of aglycon protopanaxadiol via compound K by a thermostable β-glycosidase from Pyrococcus furiosus.

Journal: Applied microbiology and biotechnology 20110201

Title: Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities.

Journal: Bioorganic & medicinal chemistry letters 20110201

Title: Synthesis of protopanaxadiol derivatives and evaluation of their anticancer activities.

Journal: Anti-cancer drugs 20110101

Title: Synthesis and cytotoxic activities of new fatty acid esters of 20(S)-protopanaxadiol.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20110101

Title: Anti-Obesity effects of protopanaxdiol types of Ginsenosides isolated from the leaves of American ginseng (Panax quinquefolius L.) in mice fed with a high-fat diet.

Journal: Fitoterapia 20101201

Title: 20(S)-protopanaxadiol, an active ginseng metabolite, exhibits strong antidepressant-like effects in animal tests.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20101201

Title: Enzymatic preparation of 20(S, R)-protopanaxadiol by transformation of 20(S, R)-Rg3 from black ginseng.

Journal: Phytochemistry 20100901

Title: [Preparation and study in vitro of 20 (S)-protopanaxadiol pharmacosomes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100401

Title: Effect of protopanaxadiol derivatives in high glucose-induced fibronectin expression in primary cultured rat mesangial cells: role of mitogen-activated protein kinases and Akt.

Journal: Archives of pharmacal research 20100101

Title: Development of a UPLC-ESI-MS/MS assay for 20(S)-protopanaxadiol and pharmacokinetic application of its two formulations in rats.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20100101

Title: 20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells.

Journal: Planta medica 20090801

Title: Antioxidant and apoptotic effects of korean white ginseng extracted with the same ratio of protopanaxadiol and protopanaxatriol saponins in human hepatoma HepG2 cells.

Journal: Annals of the New York Academy of Sciences 20090801

Title: [Determination of content and entrapment efficiency of 20 (S)-protopanaxadiol in pharmacosomes by RP-HPLC method].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090501

Title: [Preparation and isolation on the rare ginsenoside derivatives with anti-cancer activity].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090501

Title: Rapid and sensitive LC-MS/MS assay for the quantitation of 20(S)-protopanaxadiol in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090215

Title: Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells.

Journal: British journal of pharmacology 20090201

Title: Comparison of the antiobesity effects of the protopanaxadiol- and protopanaxatriol-type saponins of red ginseng.

Journal: Phytotherapy research : PTR 20090101

Title: Biotransformation of 20(S)-protopanaxadiol by Mucor spinosus.

Journal: Phytochemistry 20090101

Title: Sensitive determination of 20(S)-protopanaxadiol in rat plasma using HPLC-APCI-MS: application of pharmacokinetic study in rats.

Journal: Journal of pharmaceutical and biomedical analysis 20081215

Title: Pharmacokinetics of salvianolic acids after intravenous injection, with and without Panax quinquefolium protopanaxadiol saponins, in rats.

Journal: Journal of ethnopharmacology 20080522

Title: 20(S)-protopanaxadiol and the ginsenoside Rh2 inhibit Na+ channel-activated depolarization and Na+ channel-dependent amino acid neurotransmitter release in synaptic fractions isolated from mammalian brain.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20080401

Title: Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra.

Journal: Journal of natural products 20080301

Title: 20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol, a novel natural product for prostate cancer therapy: activity in vitro and in vivo and mechanisms of action.

Journal: British journal of cancer 20080226

Title: Marked production of ginsenosides Rd, F2, Rg3, and compound K by enzymatic method.

Journal: Chemical & pharmaceutical bulletin 20071001

Title: Antiestrogenic effect of 20S-protopanaxadiol and its synergy with tamoxifen on breast cancer cells.

Journal: Cancer 20070601

Title: 20S-protopanaxadiol-induced programmed cell death in glioma cells through caspase-dependent and -independent pathways.

Journal: Journal of natural products 20070201

Title: Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I.

Journal: Chemical & pharmaceutical bulletin 20070201

Title: Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice.

Journal: Vaccine 20070122

Title: Metabolite 1 of protopanaxadiol-type saponins, an axonal regenerative factor, stimulates teneurin-2 linked by PI3-kinase cascade.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20060601

Title: Ginsenoside metabolites, rather than naturally occurring ginsenosides, lead to inhibition of human cytochrome P450 enzymes.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20060601

Title: Ginsenoside 20(S)-protopanaxadiol inhibits the proliferation and invasion of human fibrosarcoma HT1080 cells.

Journal: Basic & clinical pharmacology & toxicology 20060601

Title: Natural products from ginseng inhibit [3H]batrachotoxinin A 20-alpha-benzoate binding to Na+ channels in mammalian brain.

Journal: European journal of pharmacology 20060113

Title: Anti-inflammatory activity of 20(S)-protopanaxadiol: enhanced heme oxygenase 1 expression in RAW 264.7 cells.

Journal: Planta medica 20051201

Title: [Alkaline-degradation products of ginsenosides from leaves and stems of Panax quinquefolium].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20051001

Title: High performance liquid chromatographic-mass spectrometric determination of ginsenoside Rg3 and its metabolites in rat plasma using solid-phase extraction for pharmacokinetic studies.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050425

Title: A role for the carbohydrate portion of ginsenoside Rg3 in Na+ channel inhibition.

Journal: Molecules and cells 20050227

Title: Uptake and metabolism of ginsenoside Rh2 and its aglycon protopanaxadiol by Caco-2 cells.

Journal: Biological & pharmaceutical bulletin 20050201

Title: Liquid chromatography/tandem mass spectrometry for pharmacokinetic studies of 20(R)-ginsenoside Rg3 in dog.

Journal: Rapid communications in mass spectrometry : RCM 20050101

Title: The inhibitory effect of intestinal bacterial metabolite of ginsenosides on CYP3A activity.

Journal: Biological & pharmaceutical bulletin 20041001

Title: Abeta(25-35)-induced memory impairment, axonal atrophy, and synaptic loss are ameliorated by M1, A metabolite of protopanaxadiol-type saponins.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20040501

Title: Ginsenosides 20(S)-protopanaxadiol and Rh2 reduce cell proliferation and increase sub-G1 cells in two cultured intestinal cell lines, Int-407 and Caco-2.

Journal: Canadian journal of physiology and pharmacology 20040301

Title: Mechanistic studies on protopanaxadiol, Rh2, and ginseng (Panax quinquefolius) extract induced cytotoxicity in intestinal Caco-2 cells.

Journal: Journal of biochemical and molecular toxicology 20040101

Title: Degradation of ginsenosides in humans after oral administration.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030801

Title: Axonal and dendritic extension by protopanaxadiol-type saponins from ginseng drugs in SK-N-SH cells.

Journal: Japanese journal of pharmacology 20021101

Title: Ginsenosides protect apical transporters of cultured proximal tubule cells from dysfunctions induced by h(2)o(2).

Journal: Kidney & blood pressure research 20020101

Title: Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice.

Journal: Journal of ethnopharmacology 19990801

Title: iu Y, Yang G, Bu X, et al. Cell-type-specific regulation of raft-associated Akt signaling. Cell Death Dis. 2011;2(4):e145. Published 2011 Apr 14.

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Tags:30636-90-9 Molecular Formula|30636-90-9 MDL|30636-90-9 SMILES|30636-90-9 Dammar-24-ene-3,12,20-triol, (3β,12β)-